Ammonia → HCID 57743032, compound

Participants

Reaction Conditions

Reaction Steps

In a 250 ml, three-necked flask fitted with a magnetic stirrer under inert atmosphere, 20 ml of liquid ammonia is condensed and sodium is added until the solution turns blue. A solution of 1-[(1-benzyl-1H-pyrazol-4-yl)methyl]-4-(2,3,5-trifluorophenyl)pyrrolidin-2-one 160 (1 g, 2.6 mmol) in THF (5 ml) is added and the mixture is stirred at −78° C. for 5 minutes. NH4Cl and water are added, ammonia is evaporated in vacuo and the aqueous phase is extracted with CH2Cl2. The combined organic phases are washed with brine, dried over MgSO4, filtered and concentrated to dryness. The residue is purified by preparative chromatography on C18 reversed phase (CH3CN/H2O/NH4HCO3, gradient) to afford 73 mg of 4-phenyl-1-(1H-pyrazol-4-ylmethyl)pyrrolidin-2-one 162.

Provenance & Evidence